Chapter 13: Q13-25E (page 419)
How many absorptions would you expect the following compound tohave in its 1H and 13C NMR spectra?
Chapter 13: Q13-25E (page 419)
How many absorptions would you expect the following compound tohave in its 1H and 13C NMR spectra?
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Get started for freeAssume that you have a compound with the formula C3H6O .
(a) How many double bonds and/or rings does your compound
contain?
(b) Propose as many structures as you can that fit the molecular
formula.
(c) If your compound shows an infrared absorption peak at 1715cm-1,
what functional group does it have?
(d) If your compound shows a single 1H NMR absorption peak at 2.1,
what is its structure?
Compound D is isomeric with compound C (Problem 13-61) and has the following NMR spectral data. Propose a structure.
Compound D Broadband-decoupled NMR: 9.7, 29.9, 74.4, 114.4, 141.4 d DEPT-90: 74.4, 141.4 d DEPT-135: positive peaks at 9.7, 74.4, 141.4 d; negative peaks at 29.9, 114.4 d
Compound A, a hydrocarbon with = 96 in its mass spectrum, has the spectral data given below. On reaction with , followed by treatment with basic , A is converted into B, whose spectral data are also given below. Propose structures for A and B.
Compound A Broadband-decoupled NMR: 26.8, 28.7, 35.7, 106.9, 149.7 d DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at 26.8, 28.7, 35.7, 106.9 d
Compound B Broadband-decoupled NMR: 26.1, 26.9, 29.9, 40.5, 68.2 d DEPT-90: 40.5 d DEPT-135: positive peak at 40.5 d; negative peaks at 26.1, 26.9, 29.9, 68.2 d
Carboxylic acids react with alcohols (R'OH) in the presence of an acid catalyst. The reaction product of propanoic acid with methanol has the following spectroscopic properties. Propose a structure.
MS: = 88
IR: 1735
NMR: 1.11 (3 H, triplet, J 5 7 Hz); 2.32 (2 H, quartet, J 5 7 Hz); 3.65 (3 H, singlet) NMR: 9.3, 27.6, 51.4, 174.6
Question: The mass spectrum and NMR spectrum of a hydrocarbon are shown. Propose a structure for this hydrocarbon, and explain the spectral data.
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